With a deal with Snoop Dogg in the works, the rapper was about to hit hip-hop heaven. Now he faces decades behind bars. But is he guilty?

That dude you could buy weed from at 2 a.m. That dude with gang life written all over his face. That dude every hoodrat had a crush on. That dude who just might rob you. That dude who was good at shaking off haters but even better at getting in his own way.

That dude who could rap.

Ruben Martinez

G-Rider

Ruben Martinez

Behind the thick prison glass of a visitor's telephone stall in Central Men's Jail in Santa Ana, his street-earned swagger is still visible, though noticeably deflated. A calm aura floats faintly over frayed cornrows and broad cheekbones accented with ink: a devil's pitchfork on the right, two teardrops on the left. The color in his skin is muted by the carrot-purée-colored jump suit. I was probably the last familiar face he'd expected to see on the other side of a jail phone at 9:30 a.m. on a Sunday; his eyelids had jumped a little as I came around the corner, a surprised smile sweeping across a scruffy jaw that hadn't been shaved in days.

"Ah, damn!" he says, laughing. "Hey, man! How'd you know I was here?"

His tone is hushed and raspy, but for someone potentially facing 23 years in prison, he seems surprisingly upbeat.

The last time I'd seen Kadillak was Oct. 12, 2012, the night before he was to perform at Sound Asylum, a quarterly hip-hop residency at Costa Mesa's Detroit Bar. We'd sat down for an interview at the Crosby on a dead night in downtown Santa Ana to talk about his forthcoming album, Late Nights, Early Money, which he'd planned to release in the coming weeks. Off the record, he'd told me he'd been ducking Orange County Sheriff's deputies for a little more than a month. Kadillak never showed up for the gig. Two days after that, he was arrested for carjacking and second-degree robbery.

Kadillak adamantly professes his innocence, insisting he simply got into an argument with his ex-girlfriend and boneheadedly parked her car down the street without telling her. On the one hand, there's no such thing as a guilty man behind bars. On the other hand, his story doesn't quite add up. He already has two felony strikes on his record. And what kind of innocent man runs from the law?

"What rapper really wants to end their show in handcuffs?" he says. "Even if it's temporary?"

But there's nothing remotely temporary about Kadillak's predicament. If convicted, he faces 23 years in state prison. Now he's that dude who almost became a famous rapper, only to have his dreams of flying high in the hip-hop world potentially scratched, chopped and screwed, his ultimate fate soon to be in the hands of a jury of his peers. His public defender has warned him the jury is likely to be all-white; he was told he looks the part of a carjacker.

But Kadillak insists he has no choice but to move forward.

"I just know I've come so far from where I was, and I'm too close to the life I've been hustling toward for years," he says. "If I go back to prison, I can't take it this time. It will break me."

* * *

Three months ago, the rapper born Deron Hollins was closer than he'd ever been to being discovered. Kadillak was rubbing elbows with Snoop Dogg and had just begun negotiating a recording contract with his label, Doggystyle Records. He was putting out his third album, which had the potential to be more than just a street-level hit. After more than 15 years as a rapper and a life of hard knocks, drug dealing, multiple arrests and two convictions, things were starting to come together for him. The question is whether the 33-year-old rapper's hip-hop career breakthrough could be over just as it's about to start.

Kadillak's current predicament began on Oct. 15, 2012. At 2 p.m, he found himself behind the wheel of his new girlfriend's black Chevy Monte Carlo, which was being swarmed by cops. He'd just rolled up to her apartment complex in Mission Viejo to return the car so she could pick up her son from school. Before he'd even parked, his guts were churning in his stomach. Something in the back of his mind told him things weren't going to end well for him that day. Since September, he'd known he was a wanted man.

His arrest warrant stemmed from a phone call to Tustin police placed by an ex-girlfriend, who initially called them Aug. 16, after a public shouting match outside a friend's computer-repair business. Kadillak used to rent a suite across from the complex, a place he called Skyballin Studios, and still occasionally visited his friend. They argued over $3,500 she'd taken from his wallet the night before, shortly after she examined his cell phone and discovered he'd been seeing other women behind her back.

Though she returned a day later with the money, an argument ensued over the fact that the ex found one of Kadillak's female friends taking a nap in one of the office rooms at the repair shop. She ended up bolting out of the studio through the middle of the complex to hide out in an area near the rental office.